CN102795974A - Liquid crystal medium and liquid crystal composition - Google Patents
Liquid crystal medium and liquid crystal composition Download PDFInfo
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- CN102795974A CN102795974A CN2012102698983A CN201210269898A CN102795974A CN 102795974 A CN102795974 A CN 102795974A CN 2012102698983 A CN2012102698983 A CN 2012102698983A CN 201210269898 A CN201210269898 A CN 201210269898A CN 102795974 A CN102795974 A CN 102795974A
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- 239000004973 liquid crystal related substance Substances 0.000 title claims abstract description 59
- 150000001875 compounds Chemical class 0.000 claims abstract description 103
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 27
- 238000003756 stirring Methods 0.000 claims description 23
- 229910052799 carbon Inorganic materials 0.000 claims description 15
- 150000001721 carbon Chemical group 0.000 claims description 13
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 12
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 8
- 239000004327 boric acid Substances 0.000 claims description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical class CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 150000002978 peroxides Chemical class 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 6
- 210000002858 crystal cell Anatomy 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 235000015320 potassium carbonate Nutrition 0.000 claims description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
- 235000007715 potassium iodide Nutrition 0.000 claims description 4
- 229960004839 potassium iodide Drugs 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- VVWRJUBEIPHGQF-MDZDMXLPSA-N propan-2-yl (ne)-n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)\N=N\C(=O)OC(C)C VVWRJUBEIPHGQF-MDZDMXLPSA-N 0.000 claims description 3
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 2
- 239000007818 Grignard reagent Substances 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- 150000004795 grignard reagents Chemical class 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 6
- 230000003287 optical effect Effects 0.000 abstract description 9
- 230000004044 response Effects 0.000 abstract description 8
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 4
- 230000008901 benefit Effects 0.000 abstract description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- 239000000463 material Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 9
- 238000003810 ethyl acetate extraction Methods 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000012071 phase Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 125000005843 halogen group Chemical group 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000001819 mass spectrum Methods 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000004440 column chromatography Methods 0.000 description 4
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical compound OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 0 CC*C1=CC(CC(*)C2)C2C=C1 Chemical compound CC*C1=CC(CC(*)C2)C2C=C1 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910021417 amorphous silicon Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 229910021419 crystalline silicon Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000013213 extrapolation Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 239000012212 insulator Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 238000005304 joining Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920005591 polysilicon Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
Images
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Liquid Crystal Substances (AREA)
Abstract
The invention provides compounds having a general formula (I), used as a component of a liquid crystal medium and having an indene ring structure as well as a preparation method and application of the compounds. The compounds are negative liquid crystal compounds, and have the advantages of high dielectric and anisotropic absolute value, proper optical anisotropy, high clearing point and wide nematic phase temperature range; and a display using the compounds can have high response speed and wide working range, and can be well displayed in various environments. The invention also provides a liquid crystal composition comprising one or more of the compounds and a liquid crystal element comprising the liquid crystal composition.
Description
Technical field
The present invention relates to the compound that contains the indenes ring structure as the component of negative liquid crystal medium
Background technology
For liquid crystal display device; Display format according to liquid crystal is divided into PC (phase change; Phase transformation), TN (twist nematic, twisted-nematic), STN (super twisted nematic, supertwist is to row), ECB (electrically controlled birefringence; Electrically conerolled birefringence), OCB (optically compensated bend; Optical compensation curved), IPS (in-plane switching, coplane change), VA types such as (vertical alignment, vertical orientations).Type of drive according to element is divided into PM (passive matrix, passive-matrix) type and AM (active matrix, active-matrix) type.PM is divided into static state (static) and multichannel types such as (multiplex).AM is divided into TFT (thin film transistor, thin film transistor), MIM types such as (metal insulator metal, metal-insulator-metals).The type of TFT has non-crystalline silicon (amorphous silicon) and polysilicon (polycrystal silicon).The latter is divided into high temperature modification and low temperature modification according to ME.Liquid crystal display device is divided into the reflection-type of utilizing natural light, utilizes infiltration type backlight and utilize natural light and the semi-transmission type of two kinds of light sources backlight according to the type of light source.
Use TN effect the most generally, STN effect and SBE (supertwist double refraction) effect in these effects.In these electrooptic effects electrooptic effect similar, all use the liquid crystal media of positive dielectric anisotropy with it.Except the electrooptic effect of the liquid crystal media of the positive dielectric anisotropy of use mentioned; The electrooptic effect that also has other the liquid crystal media that utilizes negative dielectric anisotropic; ECB (electrically conerolled birefringence) effect and its sub-form DAP (joining distortion in opposite directions) effect for example, VAN effect and CSH (the ultra vertical plane of colour) effect.
Liquid crystal material must have good chemistry and thermostability and to the good stability of electric field and electromagnetic radiation.In addition, liquid crystal material should have LV and short response time, low threshold voltage and high-contrast.And the optical anisotropy of compsn is associated with the contrast gradient of element.
In the large scale liquid crystal TV, thin film transistor (TFT) display format of liquid crystal molecule arranged vertical (VA) is used widely in recent years.Its advantage is that the visual angle is wide, response speed fast, contrast gradient is bigger.Traditional distortion-nematic-mode (TN) uses dielectric anisotropy to be (Δ ε=ε ∥-ε ⊥ just; Δ ε＞0) liquid crystal material; On the molecular long axis direction, have polar group, make long axis direction specific inductivity (ε ∥) greater than perpendicular electric constant (ε ⊥); And the liquid crystal material that the VA pattern requires to be adopted has bigger dielectric anisotropy of negativity value (Δ ε < 0) and bigger optical anisotropy (Δ n).
In liquid-crystal display, require the WV of indicating meter should be low as much as possible, thereby need have the liquid crystal media of big dielectric anisotropy absolute value.
In order to ensure the characteristic of satisfied quality, particularly low voltage, in the VA-TFT indicating meter; Need have big dielectric anisotropy absolute value, appropriate optical anisotropy, low viscosity; Wide operating temperature range; High response speed, good chemicalstability, the material of good ultraviolet light stability and good mutual solubility.
As everyone knows; The anisotropic liquid crystal compound is the liquid crystal material of negative dielectric anisotropic particularly; Its compound molecule majority is formed by the substituted aromatic nucleus of halogen, trifluoromethyl or cyanic acid by 2,3; Link to each other with covalent linkage between the aromatic ring when needed, contain one or more side direction group in the general formula molecule, these side direction groups are cyanic acid or nitro normally.
The liquid-crystal compsn that in German patent DE 2240864, DE2613293 and DE2835662, has related to this type of negative dielectric anisotropic, they have negative dielectric anisotropy (Δ ε).
The negative dielectric anisotropic liquid crystal compound that is expressed from the next has been described in Chinese patent CN1454890
Yet these negative liquid crystal materials have very weak negative dielectric anisotropic.
The research and development in liquid crystal material field still shoulder heavy responsibilities, and in order to improve the character of liquid crystal cell, exploitation that efforts still need to be can be optimized the novel cpd of liquid-crystal display.
Therefore, the object of the present invention is to provide and have the compound that premium properties is used for liquid crystal media.This compound has negative dielectric anisotropic, is particularly suitable in the VA display format, can satisfy liquid crystal cell to big dielectric anisotropy absolute value; The appropriate optical anisotropy; Low viscosity, wide operating temperature range, high response speed; Good chemicalstability, good ultraviolet light stability and good requirements such as mutual solubility.
Summary of the invention
The purpose of this invention is to provide a kind of compound that contains the indenes ring structure that can be used as the component of liquid crystal media, this compound can be used as the negative liquid crystal material.
Another object of the present invention provides the above-mentioned preparation method who contains the compound of indenes ring structure.
Another purpose of the present invention provides a kind of said liquid-crystal compsn that contains the compound of indenes ring structure that comprises.
A purpose more of the present invention provides a kind of liquid crystal cell that comprises said liquid-crystal compsn as integrant.
One aspect of the present invention provides a kind of compound that contains the indenes ring structure that can be used as the component of liquid crystal media, and this compound has the structure shown in the logical formula I:
Wherein,
R
1And R
2Identical or different, independently represent H, halogen, halo or unsubstituted alkyl or alkoxyl group separately or have halo or the unsubstituted alkane thiazolinyl or the alcoxyl thiazolinyl of 2-15 carbon atom with 1-15 carbon atom, wherein, at said R
1And R
2In one or more-CH
2-group can be independently of one another by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-substitutes, its prerequisite is that Sauerstoffatom directly is not connected to each other;
Ring
ring
is identical or different, is independently from each other the group that
forms separately;
Z
1And Z
2Identical or different, be independently from each other separately by carbon-carbon single bond and-CO-O-,-O-CO-,-CF
2O-,-CH
2O-,-CH
2CH
2-,-CF
2CH
2-,-CF=CF-,-CH=CH-,-CH=CF-,-C
2F
4-the group formed with-C ≡ C-;
Z is independently selected from by-OCH
2CH
2O-,-(CH
2)
4-,-OCF
2CF
2The group that O-forms,
M and n are identical or different, are independently from each other 0,1 or 2 separately; And 0≤m+n3.
In some embodiments, R
1And R
2Independently represent H, F, halo or unsubstituted alkyl or alkoxyl group separately or have halo or the unsubstituted alkane thiazolinyl or the alcoxyl thiazolinyl of 2-10 carbon atom with 1-10 carbon atom, wherein, at said R
1And R
2In one or more-CH
2-group can be independently of one another by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-substitutes, its prerequisite is that Sauerstoffatom directly is not connected to each other.Preferably, R
1And R
2The alkyl of representing 1-5 carbon atom independently of one another.
In some embodiments, Z
1And Z
2Identical or different, be independently from each other separately by-CO-O-,-O-CO-,-CF
2O-,-CH
2O-,-CH
2CH
2-,-CF
2CH
2-,-CF=CF-,-CH=CH-,-group that C ≡ C-and carbon-carbon single bond are formed;
In some embodiments, Z is independently selected from by-OCF
2CF
2O-or-OCH
2CH
2The group that O-forms;
In some embodiments, m and n are identical or different, are independently from each other 0 or 1 separately; And 0≤m+n≤2.
Preferably, compound of the present invention is selected from the group of being made up of following compound:
Wherein,
R
1And R
2Independently represent H, F, halo or unsubstituted alkyl or alkoxyl group separately or have halo or the unsubstituted alkane thiazolinyl or the alcoxyl thiazolinyl of 2-10 carbon atom with 1-10 carbon atom, wherein, at said R
1And R
2In one or more-CH
2-group can be independently of one another by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-substitutes, its prerequisite is that Sauerstoffatom directly is not connected to each other.
Another aspect of the present invention provides a kind of method for preparing compound of the present invention, comprises the steps:
1) in solvents tetrahydrofurane, at N
2Under the protection, with the compound of general formula 1
(general formula 1)
With the reaction of magnesium powder, generate the Grignard reagent of general formula 2
At-30 ℃--10 ℃, drip boric acid three isobutylates to above-mentioned reaction system, dropwise stirring at room reaction 0.5-4h, obtain the compound of general formula 3;
2) in dichloromethane solvent, under the room temperature, with the compound and 30% ydrogen peroxide 50 of general formula 3, stirring reaction 2-8h obtains the compound of general formula 4;
3) in tetrahydrofuran solvent, at room temperature, N
2Protection down, with compound, ethylene chlorhydrin, triphenylphosphine, the diisopropyl azodiformate of general formula 4, stirring reaction 1-16h obtains the compound of general formula 5;
4) in tetrahydrofuran solvent, at-78 ℃, N
2Protection down adds compound, n-Butyl Lithium, boric acid three isobutylates of general formula 6, reinforced finishing, and under the room temperature, 0.5-2h obtains the compound of general formula 7;
5) in dichloromethane solvent, under the room temperature, with the compound and 30% ydrogen peroxide 50 of general formula 7, stirring reaction 1-14h obtains the compound of general formula 8;
6) under 80 ℃-100 ℃, the compound of general formula 5, the compound of general formula 8, salt of wormwood, potassiumiodide, N, the N-NMF, stirring reaction 0.5-8h obtains the compound of formula I;
Wherein, R
1, R
2, the ring
Ring
Z
1, Z
2, Z and m have and aforementioned identical definition with n.
Another aspect of the present invention provides a kind of liquid-crystal compsn, comprises a kind of or more kinds of compound of the present invention.
Another aspect of the present invention provides a kind of liquid crystal cell that comprises said liquid-crystal compsn.
Other liquid crystalline cpds of liquid crystalline cpd and prior art shown in the logical formula I provided by the invention are compared, and have big dielectric anisotropy absolute value (Δ ε), very big optical anisotropy (Δ n), low rotary viscosity (γ
1), the nematic temperature range of high clearing point (Cp) and broad, their chemical property all are stable; Prepare in the process at logical formula I, raw material is easy to get, and synthetic route is simple, is fit to large-scale industrial production, is beneficial to as showing with liquid crystal material and uses the time of response (promptly reducing rotary viscosity) that can be used for improving liquid-crystal compsn; Lifting is to the survivability of light, heat; Enlarge operating temperature range.
Description of drawings
Fig. 1 is the mass spectrum of compound 3IO2OWO2.
Fig. 2 is the nuclear magnetic spectrogram of compound 3IO2OWO2.
Fig. 3 is the mass spectrum of compound 2IO2OWO2.
Fig. 4 is the nuclear magnetic spectrogram of compound 2IO2OWO2.
Fig. 5 is the mass spectrum of compound 3IO2OWP3.
Fig. 6 is the nuclear magnetic spectrogram of compound 3IO2OWP3.
Embodiment
Below will combine specific embodiments that the present invention is described.Need to prove that following embodiment is an example of the present invention, only be used for explaining the present invention, and be not used for limiting the present invention.Under the situation that does not depart from purport of the present invention or scope, can carry out the present invention and conceive interior other combination and various improvement.
The code name of writing a Chinese character in simplified form of each test event is expressed as respectively in following examples:
Cp (℃) clearing point (to row-isotropic phase transition temperature)
Δ n optical anisotropy (589nm, 20 ℃)
Δ ε dielectric anisotropy (1KHz, 25 ℃)
Wherein, the specific refractory power anisotropy use Abbe refractometer under sodium lamp (589nm) light source, 20 ℃ test; The dielectric testing cassete is the TN90 type, the thick 7 μ m of box.
Reagent used in the present invention and other raw materials are commercially available commercial materials.
For ease of expressing, the unit structure of following liquid crystalline cpd is with the listed coded representation of table 1:
The unit structure code of table 1 liquid crystalline cpd
With following structure is example:
This structure is with the coded representation in the table 1: then can be expressed as 3PTWTP3, and for example:
Then can be expressed as nCPTPOm, the n in the code representes the C atomicity of left end alkyl, and for example n is " 3 ", representes that promptly this alkyl is-C
3H
7C in the code represents cyclohexyl; O represention oxygen atom in the code; P in the code represents phenylene; M in the code representes the C atomicity of right-hand member alkyl, and for example m is " 1 ", representes that promptly the alkyl of right-hand member is-CH
3
Monomer extrapolation testing method:
With monomer and parent liquid-crystal compsn (Δ n:0.126; Δ ε :-5.5; Cp:82.1 ℃) according to after the weight ratio 1:9 mixing, carry out performance test, calculate monomeric each item performance according to linear gauge then.
The synthetic route of the compound 3IO2OWO2 of preparation is represented as follows:
Its concrete process step is following:
1) 3IO2OWO2-2's is synthetic
The Mg powder and the 0.05g iodine that add 5.76g in the 500mL there-necked flask, 10mL THF (THF), nitrogen protection.In the 200mL tetrahydrofuran solution, slowly the tetrahydrofuran solution with the compound of 3IO2OWO2-1 (commercially available midbody) adds to above-mentioned reaction system, after question response causes with the compound dissolution of the 3IO2OWO2-1 of 47.6g; Continue the tetrahydrofuran solution of the compound of the remaining 3IO2OWO2-1 of dropping, drip and finish the little backflow 3h that boils of maintenance system; Be cooled to room temperature; Be cooled to-30 ℃, controlled temperature slowly drips boric acid three isobutylate 92g stirring at room 0.5-4h at-30 ℃ ~-10 ℃.Reaction solution is used the Hydrogen chloride cancellation, ethyl acetate extraction, and organic phase is used anhydrous sodium sulfate drying, revolves dried solvent, gets white solid 33g after the sherwood oil crystallization, and yield 80% is the compound of 3IO2OWO2-2.MS:m/z:204。
2) 3IO2OWO2-3's is synthetic
The compound that adds 20.4g3IO2OWO2-2 in the 250mL round-bottomed flask, 100mL methylene dichloride, 30mL30% ydrogen peroxide 50, stirring at room reaction 2-8h.Steam to remove dichloromethane solvent, add 100mL water, suction filtration, after the oven dry, white solid 17g, yield 96.6% is 3 compound.MS:m/z:176。
3) 3IO2OWO2-4's is synthetic
The compound, 4.1g2-glycol chlorohydrin, 13.5g triphenylphosphine, 11g diisopropyl azodiformate, the 100mL THF that add 8.8g3IO2OWO2-3 in the 250mL round-bottomed flask, under the nitrogen protection, stirring at room reaction 1-16h.Add 100mL water in the reaction solution, ethyl acetate extraction revolves dried organic solvent, and sherwood oil is that the moving phase column chromatography is separated, elutriant concentrate water white transparency oily thing 10g, be the compound of 3IO2OWO2-4.MS:m/z:238。
4) 3IO2OWO2-6's is synthetic
The compound that adds 7.5g3IO2OWO2-5 (commercially available midbody) in the 100mL round-bottomed flask, 30mL THF, nitrogen protection, low temperature splashes into the n-Butyl Lithium of 13mL under-78 ℃, and (n-BuLi 2.4mol/L), drips Bi Fanying 0.5-2h.Boric acid three isobutylates of 14g are dissolved among the 20mL THF, splash in the reaction system in-78 ℃, drip a Bi Ziran and rise to room temperature, stirring reaction 0.5-2h.With cancellation reaction in the reaction solution impouring Hydrogen chloride, stir 30min, ethyl acetate extraction revolves dried organic solvent, and resistates is used petroleum ether, and suction filtration gets white solid 5g, is the compound of 3IO2OWO2-6.
5) 3IO2OWO2-7's is synthetic
The compound that adds 5g3IO2OWO2-6 in the 100mL round-bottomed flask, 30mL methylene dichloride, 5mL30% ydrogen peroxide 50, stirring at room reaction 1-14h.Steam and remove dichloromethane solvent, add 50mL water, suction filtration after the oven dry, gets white solid 4.5g, is the compound of 3IO2OWO2-7.MS:m/z:174。
6) 3IO2OWO2's is synthetic
The compound, the compound of 0.73g3IO2OWO2-7,1.16g salt of wormwood, 0.07g potassiumiodide, the 10mLN that add 1g3IO2OWO2-4 in the 50mL round-bottomed flask, dinethylformamide, 80 ℃ of-100 ℃ of stirring reaction 0.5-8h.Add 50mL water in the reaction solution, ethyl acetate extraction revolves dried organic solvent, and sherwood oil is that the moving phase column chromatography is separated, elutriant concentrate white solid 1.2g, the absolute ethyl alcohol recrystallization, white needle-like crystals 1g, purity 99.5%.Make compound 8.MS:m/z:376。
1H-NMR（300MHz，CDCl
3）：7.086（1H，d）；6.787-6.719（1H，m）；6.698-6.559（3H，m）；4.351-4.256（4H，m）；4.103-4.003（2H，m）；3.030-2.931（2H，m）；2.585-2.493（2H，m）；2.675-2.483（3H，m）；1.579-1.351（7H，m）；0.962-0.915（3H，t）。
Mass spectrum and nuclear magnetic spectrogram are presented at respectively among Fig. 1 and Fig. 2.
The liquid crystal property of compound 3IO2OWO2:
Δn：0.056 Δε：-9.5 Cp：15.7
Above-mentioned same method Synthetic 2 IO2OWO2.
Mass spectrum and nuclear magnetic spectrogram are presented at respectively among Fig. 3 and Fig. 4.
Liquid crystal property:
Δn：0.069 Δε：-9.5 Cp：5.6
The synthetic route of the compound 3IO2OWP3 of preparation is represented as follows:
Its concrete process step is following:
1) 3IO2OWP3-2,3IO2OWP3-3,3IO2OWP3-4 can be with reference to the compound method of 2IO2OWO2-2,2IO2OWO2-3,2IO2OWO2-4, the compound 3IO2OWP3-1 shown in the synthetic route chart is commercially available midbody.
2) 3IO2OWP3-10's is synthetic
The compound that adds 19.2g3IO2OWP3-9 (commercially available midbody) in the 100mL round-bottomed flask, 30mL THF, nitrogen protection, low temperature splashes into the n-Butyl Lithium of 50mL under-78 ℃, and (n-BuLi 2.4mol/L), drips Bi Fanying 2h.Boric acid three isobutylates of 46g are dissolved among the 20mL THF, splash in the reaction system in-78 ℃, drip a Bi Ziran and rise to room temperature, stirring reaction 2h.With cancellation reaction in the reaction solution impouring Hydrogen chloride, stir 30min, ethyl acetate extraction revolves dried organic solvent, and resistates is used petroleum ether, and suction filtration gets white solid 8g, is the compound of 3IO2OWP3-10.
3) 3IO2OWP3-12's is synthetic
Add the compound of 9.3g3IO2OWP3-10, the compound of 11.7g3IO2OWP3-11 (commercially available midbody), 100mL glycol dimethyl ether, 35mL wet chemical (2molL in the 250mL round-bottomed flask
-1), 0.5g Tetrabutyl amonium bromide, 0.4g Pd (PPh
3)
4, nitrogen protection, back flow reaction 5h.Reaction water cancellation, ethyl acetate extraction, organic phase use anhydrous sodium sulfate drying, revolves dried solvent, sherwood oil is that the moving phase column chromatography is separated, elutriant concentrated colourless liquid 8.4g, make the compound of 3IO2OWP3-12.MS:m/z:232。
4) 3IO2OWP3-13's is synthetic
The compound that adds 4.64g3IO2OWP3-12 in the 250mL there-necked flask, 50mL THF, nitrogen protection, low temperature splashes into the hexane solution of 10mL n-BuLi (2.4mol/L) under-78 ℃, drips Bi Fanying 2h.4.6g boric acid three isobutylates are dissolved among the 10mLTHF, and-78 ℃ splash in the reaction system, drip to finish to stir 2h.In reaction solution impouring Hydrogen chloride-ice-water, stir 30min, ethyl acetate extraction revolves dried organic phase, and resistates is used petroleum ether, and suction filtration gets white solid 3g, makes the compound of 3IO2OWP3-13.
5) 3IO2OWP3-14's is synthetic
The compound that adds 13.8g3IO2OWP3-13 in the 100mL round-bottomed flask, 150mL methylene dichloride, 30mL30% ydrogen peroxide 50, stirring at room reaction 4h.Steam and remove dichloromethane solvent, add 100mL water, suction filtration after the oven dry, gets white solid 10.1g, is the compound of 3IO2OWP3-14.MS:m/z:248。
6) 3IO2OWP3's is synthetic
The compound, the compound of 1g3IO2OWP3-14,1.16g salt of wormwood, 0.07g potassiumiodide, the 10mLN that add 1g3IO2OWP3-4 in the 50mL round-bottomed flask, dinethylformamide, 80 ℃ of-100 ℃ of stirring reaction 0.5-8h.Add 50mL water in the reaction solution, ethyl acetate extraction revolves dried organic solvent, and sherwood oil is that the moving phase column chromatography is separated, elutriant concentrate white solid 1.1g, the absolute ethyl alcohol recrystallization, white needle-like crystals 0.88g, purity 99.79%.Make compound 3IO2OWP3.MS:m/z:450。
1H-NMR（300MHz，CDCl
3）：7.439-7.407（2H，m）；7.266-7.239（2H，t）；7.106-7.066（2H，m）；6.896（1H，d）；6.801（1H，s）；6.741-6.706（1H，m）；4.445-4.413（2H，m）；4.349-4.341（2H，m）；2.982-2.956（2H，m）；2.658-2.607（2H，m）；2.515-2.474（3H，m）；1.723-1.648（2H，m）；1.552-1.371（4H，m）；1.003-0.911（6H，m）。
Mass spectrum and nuclear magnetic spectrogram are presented at respectively among Fig. 5 and Fig. 6.
The liquid crystal property of compound 3IO2OWP3:
Δn：0.156 Δε：-6.5 Cp：44.4
Monomer 2PO2OWO2 and 2IO2OWO2 are dissolved in above-mentioned parent liquid-crystal compsn (Δ n:0.126 respectively; Δ ε :-5.5; Cp:82.1 ℃) after each item performance of recording, obtain the monomer performance perameter by extrapotation, as shown in table 2 below:
Table 2 liquid crystal monomer structure and test performance thereof
Monomer 3CO2OWO2 and 3IO2OWO2 are dissolved in above-mentioned parent liquid-crystal compsn (Δ n:0.126; Δ ε :-5.5; Cp:82.1 ℃) after each item performance of recording, obtain the monomer performance perameter by extrapotation, as shown in table 3 below:
Table 3 liquid crystal monomer structure and test performance thereof
From the list data of embodiment 4 and embodiment 5, can find out that compound provided by the invention is compared with compound of the same type has very big dielectric anisotropy, good optical anisotropic and suitable high clearing point.This type of liquid crystalline cpd can make the liquid-crystal display of using this compound have superior power saving performance, and response speed faster can enlarge the working range of liquid-crystal display, makes liquid-crystal display in various environment, all can keep good demonstration.
Claims (10)
1. compound with logical formula I:
Wherein,
R
1And R
2Identical or different, independently represent H, halogen, halo or unsubstituted alkyl or alkoxyl group separately or have halo or the unsubstituted alkane thiazolinyl or the alcoxyl thiazolinyl of 2-15 carbon atom with 1-15 carbon atom, wherein, at said R
1And R
2In one or more-CH
2-group can be independently of one another by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-substitutes, its prerequisite is that Sauerstoffatom directly is not connected to each other;
Ring
ring
is identical or different, is independently from each other the group that
forms separately;
Z
1And Z
2Identical or different, be independently from each other separately by carbon-carbon single bond and-CO-O-,-O-CO-,-CF
2O-,-CH
2O-,-CH
2CH
2-,-CF
2CH
2-,-CF=CF-,-CH=CH-,-CH=CF-,-C
2F
4-the group formed with-C ≡ C-;
Z is independently selected from by-OCH
2CH
2O-,-(CH
2)
4-,-OCF
2CF
2The group that O-forms,
M and n are identical or different, are independently from each other 0,1 or 2 separately; And 0≤m+n≤3.
2. according to the said compound of claim 1, it is characterized in that said R
1And R
2Independently represent H, F, halo or unsubstituted alkyl or alkoxyl group separately or have halo or the unsubstituted alkane thiazolinyl or the alcoxyl thiazolinyl of 2-10 carbon atom with 1-10 carbon atom, wherein, at said R
1And R
2In one or more-CH
2-group can be independently of one another by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-substitutes, its prerequisite is that Sauerstoffatom directly is not connected to each other.
3. according to the said compound of claim 1, it is characterized in that said Z
1And Z
2Identical or different, be independently from each other separately by-CO-O-,-O-CO-,-CF
2O-,-CH
2O-,-CH
2CH
2-,-CF
2CH
2-,-CF=CF-,-CH=CH-,-group that C ≡ C-and carbon-carbon single bond are formed.
4. according to the said compound of claim 1, it is characterized in that said Z is independently selected from by-OCF
2CF
2O-or-OCH
2CH
2O-.
5. according to the said compound of claim 1, it is characterized in that said m and n are identical or different, be independently from each other 0 or 1 separately; And 0≤m+n≤2.
6. according to the said compound of claim 1-5, said compound is selected from the group of being made up of following compound:
Wherein,
R
1And R
2Independently represent H, F, halo or unsubstituted alkyl or alkoxyl group separately or have halo or the unsubstituted alkane thiazolinyl or the alcoxyl thiazolinyl of 2-10 carbon atom with 1-10 carbon atom, wherein, at said R
1And R
2In one or more-CH
2-group can be independently of one another by-CH=CH-,-O-,-CH=CF-,-CF=CH-,-CF=CF-,-CO-O-or-O-CO-substitutes, its prerequisite is that Sauerstoffatom directly is not connected to each other.
7. according to the said compound of claim 1-5, said compound is selected from the group of being made up of following compound:
8. a method for preparing like any one described compound in the claim 1 to 7 comprises the steps:
1) in solvents tetrahydrofurane, at N
2Under the protection, with the compound of general formula 1
With the reaction of magnesium powder, generate the Grignard reagent of general formula 2
At-30 ℃--10 ℃, drip boric acid three isobutylates to above-mentioned reaction system, dropwise stirring at room reaction 0.5-4h, obtain the compound of general formula 3;
2) in dichloromethane solvent, under the room temperature, with the compound and 30% ydrogen peroxide 50 of general formula 3, stirring reaction 2-8h obtains the compound of general formula 4;
3) in tetrahydrofuran solvent, at room temperature, N
2Protection down, with compound, ethylene chlorhydrin, triphenylphosphine, the diisopropyl azodiformate of general formula 4, stirring reaction 1-16h obtains the compound of general formula 5;
4) in tetrahydrofuran solvent, at-78 ℃, N
2Protection down adds compound, n-Butyl Lithium, boric acid three isobutylates of general formula 6, reinforced finishing, and under the room temperature, 0.5-2h obtains the compound of general formula 7;
(general formula 6)
(general formula 7)
5) in dichloromethane solvent, under the room temperature, with the compound and 30% ydrogen peroxide 50 of general formula 7, stirring reaction 1-14h obtains the compound of general formula 8;
6) under 80 ℃-100 ℃, the compound of general formula 5, the compound of general formula 8, salt of wormwood, potassiumiodide, N, the N-NMF, stirring reaction 0.5-8h obtains the compound of formula I;
9. a liquid-crystal compsn comprises a kind of or more kinds of like each the described compound in the claim 1 to 8.
10. liquid crystal cell that comprises liquid-crystal compsn as claimed in claim 9.
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